Throughout the weekend, one thing the comedians at Clusterfest seemed to agree on was that a festival focused on comedy usually doesn’t work. During his headlining set on Sunday night, Daily Show alum Jon Stewart noted that such events “usually suck” before crediting Clusterfest for bucking the trend. Fans seemed to agree, as they dashed from a South Park-themed outdoor carnival to frosty beers at the immaculately recreated Paddy’s Pub from It’s Always Sunny in Philadelphia to one of the four stages concurrently offering all manner of stand-up, podcast tapings, live reads, and musical performances.
An affinity for nostalgia played well with Clusterfest attendees, who queued-up to run the Double Dare course from Nickelodeon’s beloved game show and snap pictures atop the stair car featured on Arrested Development. As one has come to expect from any festival housed in San Francisco, the food was top notch, including booths from local favorites like Southpaw BBQ and Senor Sisig. The weekend wasn’t without its share of hiccups, including an egregiously long wait to enter on Friday afternoon and some ill-timed scheduling blenders. (How does a festival next to Silicon Valley have such an unreliable app?) On the plus side, lines for refreshments and restrooms were notably short, despite a healthy attendance each day.
However, it was the main attractions that solidified Clusterfest as a gold-standard for comedy festivals. From the first (official) live performance of Saturday Night Live alums Lonely Island to a delightfully bonkers drag queen table read of Spice World, there was no shortage of rare and worthwhile sets to fill the day.
For those unable to kick off their June with three days of side-splitting mayhem, we have a few superlatives to offer some of Clusterfest’s most memorable moments.
Worst Grandpas: Gil Faizon (Nick Kroll) and George St. Geegland (John Mulaney)
A last-minute addition to the scheduled proved to be one of the weekend’s highlights when the festival began with a McLaughlin Group-style roundtable discussion featuring two of today’s most infamous alta cockers. Dormant since their triumphant run on Broadway, the aging New York alter-egos of comedians Nick Kroll and John Mulaney welcomed a star-studded panel to discuss pressing topics like Gavin Newsom’s hair, Tamagotchis, and Faizon’s resemblance to murderer-era Phil Spector. As guests Kate Berlant, John Early, Michael Che, Joe Mande, and Jon Gabrus gamely tried to keep pace with the duo’s bizarre references and pitch-black humor, Kroll’s Faizon summed-up the set well when he noted, “If you put on a wig, you can say whatever you want.”
Best Prop Work: Jinkx Monsoon
Tasked with co-curating some programming, San Francisco Sketchfest did not disappointment. The best of their offerings was quite possibly a Saturday afternoon live reading of the Spice Girls’ batshit 1998 big screen foray, Spice World. Featuring drag royalty Alaska Thunderfuck, Jinkx Monsoon, Manila Luzon, Honey Mahogany, and D’arcy Drollinger in the title roles, the task of narration was wisely left to prima mean queen Bianca Del Rio. While Luzon’s Sporty was situated on a treadmill and Drollinger’s Baby was forced to sit on a rocking horse, no one had a bigger challenge than Monsoon as Ginger. For the entirety of the performance, she gamely tried to mount an inflatable couch emblazoned with the Union Jack. Success sadly evaded her, but the spectacle of her regularly tumbling off the unwieldy prop was almost as delightful as Del Rio’s disgust at what can best be described as a nightmarish echo chamber of accents.
Best Cameo: Michael Bolton
Given trio Andy Samberg, Jorma Taccone, and Akiva Schaffer’s fruitful run on Saturday Night Live, it wasn’t entirely surprising to see that their comedy rap group The Lonely Island was able to convince a few special guests to join them for their Friday headlining set. It was a thrill to see Chris Parnell gamely hit the stage to spit his verses from the OG viral video, “Lazy Sunday,” and everyone knew the boys from Berkeley would end their jam-packed set with an assist from T-Pain on the brilliant “I’m on a Boat.” However, it was the dulcet tones of Michael Bolton that proved to be the evening’s highlight. Hitting the stage to perform two cuts — “Incredible Thoughts” from Lonely Island’s 2016 film, Pop Star, and the blockbuster film-indebted ode “Jack Sparrow“ — Bolton took his assignment to heart and unleashed his pipes on an adoring crowd. A delightful reminder of the Lonely Island’s brilliant ability to create music that is both funny and ridiculously catchy, the sight of Bolton in a pirate hat should probably be the official logo of Clusterfest next year.
Biggest Missed Opportunity: Push Notifications for Salt-N-Pepa
Clusterfest was largely flawless, thanks to smart logistics and proactive crowd control. However, several times over the course of the weekend, the set times listed on the festival’s official app didn’t match what was actually occurring on stage. This was most obvious with beloved hip-hop trio Salt-N-Pepa. Originally listed at 3:45 p.m., the group didn’t hit the stage until 4:50 p.m. Things happen, and an hour delay isn’t the end of the world. Still, for a comedy festival to miss the chance to use their push notifications to inform fans that Salt-N-Pepa’s set was being “pushed” seems like a grievous airball on some top-notch wordplay.
Boldest Choice: Shotgunning a Surge Soda (Tie: Jon Gabrus and Mike Mitchell)
Billed as a “’90s Dance Party,” co-hosts Lauren Lapkus and Jon Gabrus made sure that the Saturday evening event was truly all that and a bag of chips. In addition to the excellent covers of Alanis Morissette, Britney Spears, and more delivered by local house band Brickhouse, the festivities also included a game of Bop It between Gabrus, Lapkus, and guest Reggie Watts and an appearance from Doughboys podcast hosts Nick Wiger and Mike Mitchell. When the latter two hit the stage with an Amazon box filled with ’90s snacks, it was only a matter of time before Gabrus and Mitchell found themselves stabbing keys into 16-ounce cans of Surge soda and shotgunning them to the delight of all. Given the caffeine content of the once-popular sugar water, let’s all say a prayer for these two funny men in hopes they survive their actions.
Most Willing to Embrace an Uncomfortable Premise: Thomas Middleditch and Ben Schwartz
On Sunday afternoon, Thomas Middleditch (Silicon Valley) and Ben Schwartz (Parks & Recreation) took the lead roles in a live-read of John Hughes’ beloved 1987 road trip film Planes, Trains & Automobiles. However, on Saturday, they hit the stage with no material whatsoever to perform as their two-man improv group, Middleditch & Schwartz. For nearly an hour, they diligently worked to extricate themselves from a premise that began with a man auditioning boys to have their portraits painted. Middleditch’s discomfort and Schwartz’s exasperated glee carried the performance, as despite their best efforts, the narrative continued to creep towards a payoff they were both clearly eager to avoid. Sometimes the best improv is watching how performers navigate a scene that has gone off the rails, and there’s arguably no pair better equipped to walk that tightrope than the preposterously charismatic Middleditch & Schwartz.
Worst Hangover Cure: Kyle Mooney
It’s one thing to live through a night of drunken buffoonery, but quite another to be forced to relive it with an audience of thousands. The latter fate befell comic Kyle Mooney, who was treated to his inaugural view of his Drunk History episode centered on airplane robber D.B. Cooper by the show’s host, Derek Waters. The premise of the show sees comedians getting royally shithoused before doing their best to recall the details of forgotten moments from history, with their words later re-created verbatim by an equally talented cast. Following the screening, Waters doubled-down by showing Mooney’s outtakes from the filming — truly a ghastly prospect for anyone who’s ever had a beer (or 10) and then been confronted with social media evidence of their escapades. Mooney took it like a champ, although an on-screen moment where he weakly says “excuse me” and then plummets headfirst into carpet is likely to live in Drunk History infamy.
Best Performance in a Non-Comedic Role: T-Pain
As noted earlier, many guests struggled to enter Clusterfest when the gates first opened on Friday afternoon. One of the casualties from this debacle was the cancellation of a 5:15 p.m. set from T-Pain. As he would later share on his Instagram, the rapper was greeted with the sight of roughly seven people, causing him to switch his set to follow The Lonely Island as the festival’s final performer. While he would’ve been justified in phoning it in or simply bailing on his set altogether, instead T-Pain set the Bill Graham stage aflame with slapping beats, impressive dance moves, and a genuine gratitude for everyone that stuck around to see him. Busting through fan favorites like “Buy U a Drank” and “Bartender,” the rapper sent everyone home buzzing on a high that only comes from the joyous adrenaline rush music performed right can provide.